
Islamorada Holidays
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Where to stay in Islamorada
Find the best Islamorada areas and neighborhoods for the activities you enjoy most. Learn more about Islamorada

Matecumbe
6 out of top 10 points of interest in this area
If you're spending some time in Matecumbe, Bud n' Mary's Dive Center and Anne's Beach are top sights worth seeing.
Top hotels in Islamorada

Chesapeake Beach Resort
83409 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is 3.968.688 ₫ per night from 17 Aug to 18 Aug
3.968.688 ₫
5.942.687 ₫ total
17 Aug - 18 Aug
includes taxes & fees
9/10 Wonderful! (1,497 reviews)
"Love staying here. Any issues we’ve had they’ve resolved quickly. Can’t wait to stay here again!"
Reviewed on 11 Aug 2025

Cheeca Lodge & Spa
81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is 4.177.566 ₫ per night from 19 Aug to 20 Aug
4.177.566 ₫
6.473.257 ₫ total
19 Aug - 20 Aug
includes taxes & fees
9/10 Wonderful! (1,142 reviews)
"The room we booked in the lodge with the balcony overlooking the golf course was absolutely incredible and felt private. The food quality in the hotel, however, was not very good, especially for the price"
Reviewed on 12 Aug 2025

Amara Cay Resort
80001 Overseas Hwy, Islamorada, FL
Fully refundableReserve now, pay when you stay
The price is 4.416.003 ₫ per night from 1 Sept to 2 Sept
4.416.003 ₫
6.712.071 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,231 reviews)
"Top notch all around."
Reviewed on 13 Aug 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit

Anne's Beach
4.5/5(3 reviews)
If a restful holiday is part of your travel plans, Anne's Beach might be the perfect place to visit during your trip to Islamorada.

Founders Park
3.5/5(2 reviews)
Enjoy the beautiful sunsets and explore Founders Park, a lovely green space in Islamorada. Wander through the seaside and beautiful beaches in this family-friendly area.

Florida Keys Brewing Co.
You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.